A natural crystal like substance that is formed on the cured and processed vanilla bean. It has a very sweet & pleasant aroma and a vanilla-like taste. Although over 400 chemical compounds are add to the overall taste & smell of vanilla flavor, vanillin is the most recognizable flavor.
Historical Background/Discovery:
Vanillin was first isolated as a pure substance in 1858 by Nicolas-Theodore Gobley. He obtained vanillin by dehydrating a vanilla extract to dryness & recrystallizing the resulting solids from hot water. In 1874, two German scientists named Ferdinand Tiemann & Wilhelm Haarmann deduced its chemical structure and found a synthesis for vanillin from coniferin(glucoside found in pine bark). They also founded the first industrial company that produced Vanillin using their process. As time went on people discovered more and more ways of synthesizing Vanillin.
Where is it found?
Cured Vanilla pods contain about 2% of of dry weight vanillin. It is usually visible as a white dust or "frost" on the exterior of the pod. It is also found in Leptotes bicolor, a type of orchid that is native to Paraguay and southern Brazil. Natural vanillin, in the past, was extracted from the seed pods of a Vanilla planifola, an orchid that originally was found in Mexico. Now the orchid is grown in tropical areas all over the world. Madagascar is presently the largest producer of natural vanillin.
How is it obtained?
Pods have to be cured, during this time they become deep brown & enzymes release the vanillin from the glucoside, along with hundreds of other molecules that add to the authentic vanilla aroma. You can also make vanillin. Convenient laboratories synthesis it by involving electrophilic bromination of 4-hydoxybenzaldehyde followed by copper-catalyzed methoxylation. Large-scale industrial syntheses use a classical early method that starts from eugenol.
What can it be used for?
Vanillin is used as an addictive in foods & beverages, including candies, dessert products, chocolate, ice creams, yogurts, diet shakes & soft drinks, and as an aromatic ingredient in candles, incense, potpourri & air fresheners. It is added to some wines, alcoholic liquors, toothpastes & cigarettes. It is also used in the preparation of pharmaceutical drugs to prevent seizures or reduce the severity of them, for hypertension & Parkinson's disease. It is said that vanillin can stimulate one's appetite and enhance weight gain, so they used it to treat appetite loss & feed cattle vanillin.
Importance:
Vanillin is a significant key note in many different flavors. Ice cream & chocolate industries together compromise 75% of the market for vanillin as a flavoring. It is also used largely in the fragrance industries, in perfumes, & to mask unpleasant odors & tasks in medicines. It has been used to make other chemicals & it's very important in pharmaceuticals.
Explanation of Structure/Percent Composition:
Vanillin contains ONLY covalent bonds.
Element
Atomic Mass
# of atoms
Mass Percent
Hydrogen
1.00794
8
5.300%
Carbon
12.0107
8
63.153%
Oxygen
15.9994
3
31.547%
Reaction Tendencies:
Air & Water Reactions: Slowly oxidizes on exposure to air; slightly water soluble. New esters of vanillic acid & related acids are usually formed. Vanillin can react very violently with Br2, HClO4 & potassium-tert-butoxide. It is an aldehyde and aldehydes are readily oxidized to give carboxylic acids. Flammable and/or toxic gases are created by the combination of aldehydes with azo, diazo compounds, dithiocarbamates, nitrides, and strong reducing agents. Aldehydes can react to give first peroxo acids & carboxylic acids.
Vanillin (a.k.a. 4-hydroxy-3-methoxybenzaldehyde, Vanillaldehyde, Lioxin, p-Vanillin)
By: Marlana Fuller
Raw Structure:Vanillin (a.k.a. 4-hydroxy-3-methoxybenzaldehyde, Vanillaldehyde, Lioxin, p-Vanillin)
Raw Structure:toc
Chemical Properties:
3-D Model of Compound:
What is Vanillin?
Historical Background/Discovery:
Where is it found?
How is it obtained?
What can it be used for?
Importance:
Explanation of Structure/Percent Composition:
Reaction Tendencies:
References:
Table of Contents
Chemical Properties:
Molecular Formula: C8H8O3Molar Mass: 152.14732
Melting Point: 81-83 C
Boiling Point: 285 C
Density: 1.06 g/cm²
3-D Model of Compound:
Press link, save it in your downloads & it will open up in iMOL.What is Vanillin?
A natural crystal like substance that is formed on the cured and processed vanilla bean. It has a very sweet & pleasant aroma and a vanilla-like taste. Although over 400 chemical compounds are add to the overall taste & smell of vanilla flavor, vanillin is the most recognizable flavor.Historical Background/Discovery:
Vanillin was first isolated as a pure substance in 1858 by Nicolas-Theodore Gobley. He obtained vanillin by dehydrating a vanilla extract to dryness & recrystallizing the resulting solids from hot water. In 1874, two German scientists named Ferdinand Tiemann & Wilhelm Haarmann deduced its chemical structure and found a synthesis for vanillin from coniferin(glucoside found in pine bark). They also founded the first industrial company that produced Vanillin using their process. As time went on people discovered more and more ways of synthesizing Vanillin.Where is it found?
Cured Vanilla pods contain about 2% of of dry weight vanillin. It is usually visible as a white dust or "frost" on the exterior of the pod. It is also found in Leptotes bicolor, a type of orchid that is native to Paraguay and southern Brazil. Natural vanillin, in the past, was extracted from the seed pods of a Vanilla planifola, an orchid that originally was found in Mexico. Now the orchid is grown in tropical areas all over the world. Madagascar is presently the largest producer of natural vanillin.How is it obtained?
Pods have to be cured, during this time they become deep brown & enzymes release the vanillin from the glucoside, along with hundreds of other molecules that add to the authentic vanilla aroma. You can also make vanillin. Convenient laboratories synthesis it by involving electrophilic bromination of 4-hydoxybenzaldehyde followed by copper-catalyzed methoxylation. Large-scale industrial syntheses use a classical early method that starts from eugenol.What can it be used for?
Vanillin is used as an addictive in foods & beverages, including candies, dessert products, chocolate, ice creams, yogurts, diet shakes & soft drinks, and as an aromatic ingredient in candles, incense, potpourri & air fresheners. It is added to some wines, alcoholic liquors, toothpastes & cigarettes. It is also used in the preparation of pharmaceutical drugs to prevent seizures or reduce the severity of them, for hypertension & Parkinson's disease. It is said that vanillin can stimulate one's appetite and enhance weight gain, so they used it to treat appetite loss & feed cattle vanillin.Importance:
Vanillin is a significant key note in many different flavors. Ice cream & chocolate industries together compromise 75% of the market for vanillin as a flavoring. It is also used largely in the fragrance industries, in perfumes, & to mask unpleasant odors & tasks in medicines. It has been used to make other chemicals & it's very important in pharmaceuticals.Explanation of Structure/Percent Composition:
Vanillin contains ONLY covalent bonds.Reaction Tendencies:
Air & Water Reactions: Slowly oxidizes on exposure to air; slightly water soluble.New esters of vanillic acid & related acids are usually formed. Vanillin can react very violently with Br2, HClO4 & potassium-tert-butoxide. It is an aldehyde and aldehydes are readily oxidized to give carboxylic acids. Flammable and/or toxic gases are created by the combination of aldehydes with azo, diazo compounds, dithiocarbamates, nitrides, and strong reducing agents. Aldehydes can react to give first peroxo acids & carboxylic acids.
References:
http://www.chm.bris.ac.uk/motm/vanillin/vanillinh.htmhttp://www.3dchem.com/molecules.asp?ID=307#
http://www.chemspider.com/Chemical-Structure.13860434.html?rid=3e66f27b-9388-44d3-be9c-44efe04401ca
http://neurotalk.psychcentral.com/thread141117.html
http://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?cid=1183#x321
http://www.bookrags.com/research/vanillin-chmc/
http://en.wikipedia.org/wiki/Vanillin
http://www.chemicalbook.com/ChemicalProductProperty_EN_CB8262475.htm